[HorizonXP]

Enterprise software is definitely an area where there is plenty of opportunity. They're aching for good software; they pay exorbitant amounts for software that just isn't very good.

If someone can find a vertical where they can penetrate and provide real business value, they'll do well.

[btilly]

The bad state of enterprise software has been obvious for decades. The fact that it has persisted in being bad despite everyone knowing it should tell you that there are reasons why it remains bad.

Those reasons have also been widely known for many years. They boil down that enterprise software companies optimize for their ability to sell to decision makers who never actually use the software. See https://www.mail-archive.com/[e-mail]/msg001... for a detailed description. See http://futureofwork.glider.com/why-enterprise-software-sucks... for verification that this is not simply an isolated disgruntled developer's opinion.

[beat]

There's a lot of opportunity in enterprise, but it's really hard. I spent 20 years in enterprise myself before founding my own startup in that space. The sales cycle just kills you. I can have a product that would save enterprises hundreds of thousands a year, but it takes weeks, months, years to make a sale!

And modern B2C-oriented startup thinking doesn't get it. The sort of Lean/MVP/failfast thinking doesn't work so well when you're building for a half-dozen meetings spaced out over weeks, to match arcane localization requirements for the target customer. The reason startups rarely penetrate is because it's slow, hard, and painful - the sort of thing where big deep-pockets entrenched companies have a huge advantage.

Worse, young startup founders don't have the enterprise experience to grok why everything is so slow and so hard. It's easy to look from the outside and think those silly enterprise people must be stupid and/or malicious to make such an opaque maze of red tape. Hardly! The enterprise is filled with smart, committed, hardworking people who almost inevitably wind up in the same boat, across the many enterprise verticals.

Enterprise is valuable because it's expensive. It's expensive because it's really, really hard. Don't forget that.

On the other hand, if I can make it work as a founder, it's going to work huge.

[eitally]

One of the problems is the ingrained mentality that "enterprise" is defined by "if you throw enough money at the vendor, they'll add features and make changes for you." That's bollocks, in general, but because a lot of modern "good" software companies don't work that way, it's hard to make inroads.

As an example, according to a software engineer's review on Glassdoor, Concur's web app is about a million lines of classic ASP (and as a user of it, I can vouch for how crappy it is)... yet their mobile app is really slick and user-friendly. Netsuite is another company gaining momentum, with their premise essentially being that companies want an ERP that doesn't require the infrastructure or overhead that Oracle or SAP do. Netsuite, however, doesn't do the same kind of "consulting" as the big guys and you basically get what you get.

Big companies tend to be risk averse, and taking a risk on good software that can't be molded to existing business processes can sometimes mean it's not actually good software for that company ... or so the perception goes.